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WhereToStay.com knows Caribbean villas. Our villa experts live, work and play in the islands and possess personal knowledge of...

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WhereToStay.com knows Caribbean villas. Our villa experts live, work and play in the islands and possess personal knowledge of all our Caribbean villas on 28 different islands. Call us to speak with one of our Caribbean villa experts today.

$7,400

This 10 bedroom villa (all en-suite) is located in approximately 2.5 acres of beautiful tropical gardens with two swimming pools, two small natural beaches, beach pavilion, tennis court, gym, personal cinema and beautiful water garden. Le Bleu offers fabulous open style living in a superb private location and has been…

$3,000

Plantation House is a luxurious 8 bedroom Villa located in the heart of the exclusive Royal Westmoreland Golf and Country Club.
This grand, colonial style villa offers magnificent views of the Resort and the Caribbean Sea beyond.
Property ID: 91568
Additional amenities include: bbq outside (gas), group, family, great…

$2,858

Adonis is beautiful 4 bedroom, 5.5 bathroom villa that is as stylish as the woman who built it, Liz Claiborne. Adonis Villa was the first St. Barth vacation home of Ms. Claiborne and her husband Art Ortenberg, and is ensconced in lush gardens that embody the concept of a tropical getaway.
The main pavilion features a …

$4,286

Palm Beach Villa is a 5 bedroom luxury villa on St. Barts, located right on the seafront of the beach of Lorient Bay, offering incredible sea views over three Islands, and St. Martin in the distance. The villa has breathtaking views from any room in the house, including the bedrooms. It is the only beach villa to …

$10,000

This 16,000 sq. ft property is set by itself on a hill on over 2.5 acres of totally unspoiled land overlooking the turquoise ocean.
The main house features three floors that include large bedrooms and living rooms, two kitchens, spacious wooden decks, two heated pools, 6 bathrooms, graded terraces, an office and gym, …

$4,286

Villa Roxanne is a newly built villa located in Gustavia, St Barts. It has 6 bedrooms and 6 bathrooms with a pool.
It opens onto a full ocean view with sun all day long and partial sunset. If the weather is clear you can see Saba island and Statia.
Property ID: 91782
Additional amenities include: coffee maker, bbq …

$3,250

Flor de Cabrera Villa is a magnificent beachfront luxury vacation villa perfectly located on the golden sand beach of Orchid Bay Estates. Flor de Cabrera is over 18,500 square feet of thoughtfully architected and beautifully designed vacation dreams captured for your enjoyment. Each of the spacious ten (10) bedrooms …

$4,000

Villa Vitti is a stunning brand new 5 bedroom, 5,5 bathroom contemporary style St Barth villa rental offering some of the most dreamful island views and sunset views. Located on Lurin hillside, overlooking Shell Beach, this beautifully appointed villa represents a haven of peace and privacy, in walking distance to …

$3,300

Villa Mystique, reputed to be the largest villa on the island at 21,000 square feet, is home to four Grand Villa Suites, three pools and a full gym.
There is a Loft Junior Suite with a generous outdoor roof terrace and an optional Garden Suite which is perfectly suited for a guest's personal staff.
There are two …

$2,858

This 4 bedroom, 5,5 bathroom St Barths luxury villa rental, is located in the St Jean hillside, offering magnificent panoramic views of the bay.
On the main level the living room lies just off the main entrance, offering a panoramic ocean view.
Property ID: 3834
Additional amenities include: pool table, coffee maker…

$4,750

This 11 acre estate dating from 1740 is set on a ridge above the St Lucy coastline, a mere 200 paces from the beach. Re-designed in the late 70's by Oliver Messel, Fustic has great views of the Caribbean sea and the west coast.
There are 6 bedrooms, 5 with en suite bathrooms and 1 with an adjacent bathroom. There are …

$9,250

Little Whale Cay set in the heart of the Berry Islands in the Bahamas is a families paradise offering accommodations for up to 12 guests in three luxury villas, superb main beach stretching endlessly, a marina, spa facilities, gym,Â sea-viewÂ infinity edged pool, tennis court, a flotilla of boats for skiing, …

$3,572

BWH is certainly one of the most beautiful colonial properties of St Barthelemy, with an astonishing 270 degree view of the sea and a garden of 12 000 m2. An exceptional location and... an exceptional house.
First of all there is the majestic and mysterious entrance with a driveway winding through the trees taking you…

$5,357

Casa del Mar Villa is a luxurious 4 bedroom, 4 1/2 bathroom property, located on the hillside in exclusive Domaine du Levant and boasts a breathtaking view on the cliff and the ocean from most rooms. Natural pools are accessible by walk via a path along the cliff. Spacious living room with window walls and comfortable…

$2,550

Were it not for the exquisite pleasures offered by the spa, the pools, the restaurants and the glorious beach at Grace Bay at our luxury resort in the Turks and Caicos, no one would ever choose to venture outside.
Every suite and luxurious bedroom is an oasis of beauty, comfort and extraordinary style. Cool marble …

Situated on over one acre of waterfront land behind an electronic gate landscaped with tropical flowers and graceful royal, foxtail and coconut palm trees, spectacular Ã La Mer's large-scale design and execution is an artful combination of both colonial West Indies and classic St. John, incorporating French antique…

$2,900

Welcome to Villa Castellamonte del Mare,Ã¯Â¿Â½the newest and most complete private villa rental on the north coast of the Dominican Republic. Available by interview only to those with discriminating taste desiring a quiet, safe and peaceful vacation villa rental destination. This vacation villa rental, located …

Perched above the iconic rooftops of the resort's pavilions and offering magnificent 180 degree panoramic views of the bay and neighboring islands, Candor Villa offers true Caribbean charm, attentive service and a vast array of services and amenities. The most discerning travelers will find an "oasis for the senses" …

$7,858

Silver Rainbow Villa is located in the exclusive gated community of the Domaine du Levant, this brand new 5-bedroom villa is stunning and meets the needs and desires of the most discerning guests. Silver Rainbow, a 5 star property, draws its name from its primary cool silver-gray colors that together with its shades …

$6,000

Le Chateau des Palmiers, an expansive world-class estate, is the new "jewel" of the Caribbean. This one-of-a-kind chateau has embraced the spirit of the Caribbean with the elegance of a fine French hotel.
Featuring a 5-bedroom oceanside villa and a 4-bedroom gardenside villa, it presents an intimate, relaxed and …

$2,800

Perched above the iconic rooftops of the resort's pavilions and offering magnificent 180 degree panoramic views of the bay and neighboring islands, Joy Villa offers true Caribbean charm, attentive service and a vast array of services and amenities. The most discerning travelers will find an "oasis for the senses" in …

$4,429

L'Oasis, a magnificent new villa at the west end of Baie Rouge Beach, was completed during the summer of 2000. Rated "Top Deluxe", it includes a host of features and amenities not found in other villas.
The living room is a mixture of Moroccan, Indonesian and custom wicker furniture, original artwork and Mosaic, a …

$4,000

Coral House is an architectural masterpiece, influenced by the work of legendary theatrical designer, Oliver Messel and recalling the 18th century tradition of island plantation estates.
The floor plan gracefully integrates indoor and outdoor spaces permitting simple yet sophisticated living. The boundaries between …

$4,286

Undoubtedly the finest property in St. Martin, "Mes Amis" sits high on the Falaise des Oiseaux: a superb cliffside location with astounding views of the ocean, the surrounding coastline and the island of Anguilla.
This magnificent residence encompasses two villas built on nearly 7 acres of beautiful coastline. The …

$4,200

Experience the very essence of privacy and luxury: An entire Caribbean private island for your exclusive useâ¦ no other guests, just you and our attentive but discreet staff. Whether you wish to get away from it all, celebrate your love in private, or live life to the fullest with your friends, Royal Belize is the…

$2,572

Baraka Point is an exclusive beachfront estate offering barefoot luxury, full resort amenities and excellent service from a dedicated staff of seven.
Sitting peacefully on a headland in the Caribbean Sea with 280 Âº views, the property enjoys a built-in sense of privacy from the spectacular reef that extends across …

$39,000

With more than 150 acres of unspoiled tropical environment, 7 sparkling white sugar-sand beaches, crystal clear turquoise waters, superb elegant accommodations, and a staff of thirty-plus to attend to your every need, Musha Cay is available for exclusive and private use by you and 23 of your guests for a total of 24, …

$65,000

Surrounded by the sparkling blue Caribbean sea of the British Virgin Islands, Necker Island exudes the elegance and lifestyle of the rich and famous. You can "rent" the whole island for yourself and your guests, staying in the cliff-side villas with your own pool and never-ending views to the sea. Virgin Atlantic …

$4,950

* The Residence: A five-bedroom main residence and two three-bedroom guest villas, which can be rented individually or together. Each villa features bedrooms with en-suite bathrooms, spacious living/dining areas, sun decks with private pools and direct access to the beach.
The Sanctuary: A unique beach property made …

$3,900

One of the most beautiful villas, Villa Cragmere is located in the community of Casa de Campo. Surrounded by the Caribbean Sea and lush gardens, this villas has spectacular views of Casa de Campo Marina and Saona Island. The property comes with private access to the sea (stairs) and a master bedroom separate from the …

$5,214

Nestled into the hillside in the exclusive private enclave of Terres Basses and just 20 mins from an international airport, Sandyline is a newly completed world class, privately owned estate perfectly designed for entertaining. Overlooking the Caribbean Sea amid verdurous gardens, this property presents the perfect …

$3,700

La Belle Helene s a spectacular 11 bedroom, 10 1/2 bathroom house situated in Beau Estate below the World Heritage site of the Pitons of St. Lucia. The property is situated in an expansive, beautifully landscaped garden of 2.2 acres, with rolling lawns running down to the coast and to a rocky pebble beach. Jalousie …

$2,858

Twin Palms is perhaps the most amazing feat of architecture and design achieved in the Caribbean in decades. Fit for a king and remarkable for entertaining, the villa is designed to accommodate families and friends in extraordinary comfort and exquisite style. Unparalleled architecture and design have created one of …

$3,643

Surrounded within a lush oasis of stately Royal palms, this private 8-acre hilltop estate provides an amazing 300-degree bird's-eye view of the Virgins and miles and miles of azure sea and sky to the distant horizon. Exclusive St. Bernard's Hill House is the top of the world for those who seek privacy and a catered …

$4,571

This uniquely designed villa in the Pointe Milou area of St. Barts has been carefully planned to incorporate a modern style with lots of natural touches. This can be seen in the raw materials of wood and stone that have been used to construct this elegant villa.
The large living room flows into the dining room and …

$3,143

Built in Palladian-style adapted to the tropics, Villa BTR is a six- bedroom villa located on the west side of Pointe Milou, St Barts, with broad sunset views of Chevreaux, Fourchue, Toc Vers, St Martin and Anguilla. Elegant open-air living is enjoyed from expansive outdoor rooms and terraces, all on one level, and …

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